Growing up in the Homewood section of Pittsburgh, Wideman traveled across Pennsylvania to attend Penn on a $2,250 scholarship. After attending Peabody High School, a public and integrated school, Wideman was struck by the drastic changes in his daily life once he arrived at Penn. In his autobiographical work Brothers and Keepers, Wideman explained the transition, recounting,
I was running away from Pittsburgh, from poverty, from blackness…I’d earned a scholarship and a train ticket over the mountains to Philadelphia…If I ever doubted how good I had it…at school in that world of books, exams, pretty, rich white girls, a roommate from Long Island who unpacked more pairs of brand-new jockey shorts and T-shirts than they had in Kaufmann’s department store,…you all were back home in the ghetto to remind me how lucky I was.
In so many ways, Penn was an entirely different world for Wideman.